Sodium Carbonate → cis(+/-)-4-Chloro-N-[3-ethoxy-1-(2-oxo-1,2-dihydropyridin-4-yl)piperidin-4-yl]-5-ethyl-1H-imidazole-2-carboxamide

HRID 43726Notes

Reaction equation

HRID 43726 reaction equation
Cl.[Cl:2][C:3]1[N:4]=[C:5]([C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][NH:16][CH2:15][C@H:14]2[O:19][CH2:20][CH3:21])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9].Cl[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([OH:29])[CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O>[Cl:2][C:3]1[N:4]=[C:5]([C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][N:16]([C:23]3[CH:28]=[CH:27][NH:26][C:25](=[O:29])[CH:24]=3)[CH2:15][C@H:14]2[O:19][CH2:20][CH3:21])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 86648665cis(+/-)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochlorideHCID 178516186HCID 178516186, compound

Product 1

HCID 86648676cis(+/-)-4-Chloro-N-[3-ethoxy-1-(2-oxo-1,2-dihydropyridin-4-yl)piperidin-4-yl]-5-ethyl-1H-imidazole-2-carboxamideYield 5.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

cis(±)-4-Chloro-N-(3-ethoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride obtained in Example (131a) (100 mg, 0.297 mmol), 4-chloro-2-hydroxypyridine (46 mg, 0.36 mmol) and sodium carbonate (157 mg, 1.48 mmol) were suspended in DMSO (1 mL). The suspension was subjected to the same operation as in Example (131b) to obtain 6.3 mg of the title compound as a pale yellow amorphous solid (5%).

Sources & evidence

ORD record
ord-20bb92804b394dd3ace0fed16897d1cf
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

Loading…